November 14, 2023

From Seeking Funds to Funding Dreams

Jason Spievak's transition from entrepreneur to investor reveals a crucial perspective shift: from pursuing scarce capital to recognizing the true rarity in finding deeply committed and driven entrepreneurs, thereby altering the traditional power dynamic in the venture funding landscape.

From Seeking Funds to Funding Dreams

The journey from entrepreneur to investor, marked by a profound shift in perspective, was vividly brought to life by Jason Spievak, during a compelling dialogue at last week’s Social Symposium.

Jason, having successfully navigated the treacherous waters of startup financing, has emerged as a keen investor, offering insights into the complexities of capital and the scarcity of quality founders.

His experiences provide valuable guidance for entrepreneurs aiming to approach investors with confidence and understanding.

The Journey from Entrepreneur to Investor

Jason’s path from humble beginnings to a successful investor is a tale of resilience and determination. 

He candidly shared, "My dad drove a tow truck; he left when I was five, we were on welfare and food stamps." His early years were marked by instability, moving through four different high schools and starting out with menial jobs to make ends meet. 

From selling rugby jerseys in San Francisco to handling tedious administrative tasks, Jason's journey epitomizes the grit and perseverance needed to climb from entry-level roles to executive positions. 

This laid the groundwork for his understanding of business from the ground up and instilled in him a deep appreciation for every aspect of entrepreneurial growth.

However, it was his transition to an investor that marked a turning point. This shift wasn’t just a change in job title; it was a complete overhaul in mindset, which now allows him to speak with confidence to those just starting on their entrepreneurial path. 

The Evolution of Risk Perception

During the discussion, Jason keenly observed the audience's demographic, noting many were likely in their 30s, possibly without significant personal responsibilities like a mortgage or children. He shared, "It's not like you're walking a tightrope when you go to start your company. More like you're walking a slackline a couple feet off the ground." 

This observation speaks volumes about the evolving nature of risk across different life stages. For younger entrepreneurs, the cost of failure is often lower, making it an ideal time to take calculated risks. 

Jason's insights underscore the importance of seizing opportunities when the stakes are more manageable.

People as the Pivotal Risk and Asset

Jason went on to discuss that one of the main risks in any venture is the people involved. Recalling his experience with a bad hire, he emphasized the critical importance of the team, stating, "But the risks are really when you're bringing people onto your team." 

As an investor, he firmly believes, "The success of a company depends overwhelmingly on the founding team – probably 80 plus percent founding team and 20% the technology." 

This perspective sheds light on why investors like Jason place immense value on the people behind a startup, not just the idea.

But don’t forget that - as Jason mentioned he learned too late in life - non-technical skills like marketing, sales, finance, and smiling at somebody are actually as important as the technical skills in building successful companies.

Redefining the Startup Investment Equation

A pivotal insight from Jason’s experience is that the real scarcity in the startup world is not money but high-quality, driven founders.

Jason shared a moment of clarity that reshaped his understanding of the capital-labor relationship: "The light bulb for me was understanding that capital needs entrepreneurial labor more than labor needs capital.”

As an entrepreneur, Jason viewed capital as a scarce resource, hard to come by and fiercely competed over. However, donning the investor's hat revealed a different picture. He discovered an abundance of capital in search of high-potential ventures. 

"So I can tell you from the investor side, the money – whether it's from a venture fund, a hedge fund, private equity, or family office – without smart, energized labor, is making 1% and is losing out to inflation."

This revelation is eye-opening. It challenges the conventional narrative that funding is the primary hurdle for startups. Jason shared that investors are continually on the lookout for promising businesses, ready to invest in ideas and teams that demonstrate potential. This understanding is vital for entrepreneurs – capital is available, but the competition lies in proving one's worth.

Entrepreneurs, take note: your pitch is not just a request for funding, it's an opportunity to assert your worth and redefine the investor-entrepreneur dynamic. Your final slide should not be a mere thank you, but a bold statement of what you seek in an investor. This approach is not just about securing funds; it's about building partnerships that are grounded in mutual respect and shared vision.


Jason's transition from entrepreneur to investor reveals much about the startup funding landscape. 

The shift in perspective from viewing capital as scarce to recognizing the true scarcity of driven founders offers a fresh lens through which to view entrepreneurship. 

For entrepreneurs, this means a focus on developing qualities that attract investors – vision, drive, and authenticity. For investors, it’s about finding those rare gems that promise not just returns, but the thrill of being part of a success story. 

This understanding is crucial in fostering healthier, more productive entrepreneur-investor relationships.

Whether you are pitching your next big idea or deciding where to invest, remember the lessons from both sides of the table. 

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